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BRENDA support

Ligand L-histidine

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Basic Ligand Information

Molecular Structure
Picture of L-histidine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H9N3O2
L-histidine
HNDVDQJCIGZPNO-YFKPBYRVSA-N
Synonyms:
His, histidine, L-His, L-histidin, L-histidine[side 2]
Pathway Source
Pathways
BRENDA
histidine metabolism
KEGG
ABC transporters, Aminoacyl-tRNA biosynthesis, beta-Alanine metabolism, Biosynthesis of alkaloids derived from histidine and purine, Biosynthesis of amino acids more
MetaCyc
3-(imidazol-5-yl)lactate salvage, carnosine biosynthesis, ergothioneine biosynthesis I (bacteria), ergothioneine biosynthesis II (fungi), histamine biosynthesis more


Show all pahtways known for Show all BRENDA pathways known for L-histidine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (21 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-histidine + L-cysteine + O2 = S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
show the reaction diagram
-
acetyl-CoA + L-histidine = CoA + N-acetyl-L-histidine
show the reaction diagram
-
S-adenosyl-L-methionine + L-histidine = N-[(3S)-3-amino-3-carboxypropyl]-L-histidine + S-methyl-5'-thioadenosine
show the reaction diagram
-
L-histidine = D-histidine
show the reaction diagram
-
ATP + H2O + histidine/out = ADP + phosphate + histidine/in
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (13 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
imidazol-5-yl-pyruvate + L-glutamate = histidine + 2-oxoglutarate
show the reaction diagram
-
His-Leu + H2O = His + Leu
show the reaction diagram
-
carnosine + H2O = beta-Ala + His
show the reaction diagram
-
D-histidine = L-histidine
show the reaction diagram
-
ATP + H2O + histidine/out = ADP + phosphate + histidine/in
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (133 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-histidine + L-cysteine + O2 = S-(L-histidin-5-yl)-L-cysteine S-oxide + H2O
show the reaction diagram
-
L-histidine + H2O + NAD+ = 3-(1H-imidazol-4-yl)-2-oxopropanoate + NH3 + NADH
show the reaction diagram
-
L-His + O2 + H2O = 2-oxo-3-(1H-imidazol-4yl)-propionic acid + NH3 + H2O2
show the reaction diagram
-
L-histidine + O2 + H2O = 3-(1H-imidazol-4-yl)-2-oxopropanoate + NH3 + H2O2
show the reaction diagram
-
L-histidine + H2O + O2 = 2-oxohistidine + NH3 + H2O2
show the reaction diagram
-
L-histidine + H2O + 2 cytochrome b = 2-oxo-4-imidazolepropionic acid + NH3 + 2 reduced cytochrome b
show the reaction diagram
-
L-His + pyruvate + NADPH = N2-(D-1-Carboxyethyl)-L-His + NADP+ + H2O
show the reaction diagram
-
L-histidine + pyruvate + NADH + H+ = ?
show the reaction diagram
-
glucose 6-phosphate + L-histidine + ? = fructosyl-6-phosphate L-histidine + ?
show the reaction diagram
-
L-histidine + 2,6-dichlorophenolindophenol + H2O = ? + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
S-adenosyl-L-methionine + L-histidine = S-adenosyl-L-homocysteine + Ntau-methyl-L-histidine
show the reaction diagram
-
acetyl-CoA + L-histidine = CoA + N-acetyl-L-histidine
show the reaction diagram
-
acetyl-CoA + L-histidine = CoA + N-acetyl-L-histidine
show the reaction diagram
-
nicotinic acid mononucleotide + histidine = nicotinate + ?
show the reaction diagram
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S-adenosyl-L-methionine + L-histidine = N-[(3S)-3-amino-3-carboxypropyl]-L-histidine + S-methyl-5'-thioadenosine
show the reaction diagram
-
L-histidine + 4-(methylsulfanyl)-2-oxobutanoate = 3-((1H-imidazo)-4-yl)-2-oxopropanoate + L-methionine
show the reaction diagram
-
2-oxosuccinamic acid + L-histidine = L-asparagine + 3-(1H-imidazol-4-yl)-2-oxopropanoate
show the reaction diagram
-
L-histidine + 2-oxoglutarate = 3-(1H-imidazol-4-yl)-2-oxopropanoate + L-glutamate
show the reaction diagram
-
L-histidine + 2-oxoisohexanoate = ?
show the reaction diagram
-
L-histidine + 2-oxoglutarate = 2-oxo-3-imidazolpropanoate + L-glutamate
show the reaction diagram
-
L-histidine + 4,5-dioxopentanoate = 5-aminolevulinate + 3-(1H-imidazol-4-yl)-2-oxopropanoate
show the reaction diagram
-
L-histidine + 2-oxoglutarate = 3-(1H-imidazol-4-yl)-2-oxopropanoic acid + L-glutamate
show the reaction diagram
-
L-histidine + pyruvate = 3-(1H-imidazol-4-yl)-2-oxopropanoate + L-alanine
show the reaction diagram
-
L-histidine + glyoxylate = 3-(1H-imidazol-4-yl)-2-oxopropanoate + glycine
show the reaction diagram
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histidine + glyoxylate = 3-(1H-imidazol-4-yl)-2-oxopropanoate + glycine
show the reaction diagram
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L-histidine + glyoxylate = 3-(1H-imidazol-4-yl)-2-oxopropanoate + glycine
show the reaction diagram
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L-histidine + a 2-oxo acid = ?
show the reaction diagram
-
His = ?
show the reaction diagram
-
Histidine = Histamine + CO2
show the reaction diagram
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L-histidine + L-serine = ?
show the reaction diagram
-
L-histidine = D-histidine
show the reaction diagram
-
ATP + L-tyrosine + histidine = ? + AMP
show the reaction diagram
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ATP + L-Arg + L-His = ADP + phosphate + L-Arg-L-His
show the reaction diagram
-
ATP + H2O + histidine/out = ADP + phosphate + histidine/in
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (81 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
alpha-N-methyl-L-histidine + O2 + H2O = L-histidine + formaldehyde + H2O2
show the reaction diagram
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5-L-glutamyl-L-His + Gly-Gly = L-His + 5-L-glutamyl-Gly-Gly
show the reaction diagram
-
L-histidine-7-amido-4-methylcoumarin + H2O = L-histidine + 7-amino-4-methylcoumarin
show the reaction diagram
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L-His-2-naphthylamide + H2O = L-His + 2-naphthylamine
show the reaction diagram
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HSDAVFTDNYTRLRKQMAVKKYLNSILN + H2O = His + SDAVFTDNYTRLRKQM + AVKKYLN + SILN
show the reaction diagram
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beta-Ala-L-His + H2O = beta-Ala + L-His
show the reaction diagram
-
L-His-2-naphthylamide + H2O = L-His + 2-naphthylamine
show the reaction diagram
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L-Ala-L-His + H2O = L-Ala + L-His
show the reaction diagram
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L-Asp-L-His + H2O = L-Asp + L-His
show the reaction diagram
-
His-Pro + H2O = His + Pro
show the reaction diagram
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benzyloxycarbonyl-Phe-His + H2O = benzyloxycarbonyl-Phe + His
show the reaction diagram
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L-Bz-His + H2O = benzoic acid + L-histidine
show the reaction diagram
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Ac-Asp-Arg-Val-Tyr-Ile-His-Pro-Phe-His + H2O = Ac-Asp-Arg-Val-Tyr-Ile-His-Pro-Phe + L-histidine
show the reaction diagram
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Ac-Asp-Arg-Val-Tyr-Ile-His-Pro-Phe-His + H2O = Ac-Asp-Arg-Val-Tyr-Ile-His-Pro-Phe + L-histidine
show the reaction diagram
-
2-aminobenzoyl-Phe-Arg-His + H2O = 2-aminobenzoyl-Phe-Arg + His
show the reaction diagram
-
pyroglutamyl-His + H2O = pyroglutamate + His
show the reaction diagram
-
beta-Asp-His + H2O = Asp + His
show the reaction diagram
-
L-His-4-nitroanilide + H2O = L-His + 4-nitroaniline
show the reaction diagram
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N-benzyloxycarbonyl-Gly-Pro-His + H2O = N-benzyloxycarbonyl-Gly-Pro + L-His
show the reaction diagram
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His-Leu + H2O = Histidine + leucine
show the reaction diagram
-
N-acetyl-L-histidine + H2O = acetate + L-histidine
show the reaction diagram
-
Nalpha-benzyloxycarbonyl-L-His + H2O = benzyl alcohol + CO2 + L-His
show the reaction diagram
-
D-histidine = L-histidine
show the reaction diagram
-
ATP + H2O + histidine/out = ADP + phosphate + histidine/in
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (42 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
stimulation
-
activates
-
histidine-HCl buffer results in considerably higher activity than corresponding bisTris-HCl or Tris-HCl buffers
-
activates in presence of 3 M NaCl, 3 M Kcl or in absence of salts
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increases enzyme production
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activates, activation negated by metal ions
-
stimulatory effect
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activation in a concentration dependent manner
-
activation
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activation
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activation
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stimulates
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50 mM, stimulates
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induction and activation
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activating ability in decreasing order: histamine, imidazole, L-histidine, D-histidine
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stimulates
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152% activity at 1 mM
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required, maximal activation at 10 mM
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Inhibitor in Enzyme-catalyzed Reactions (81 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
19% inhibition at 10 mM
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10 mM histidine reduces activity by 19%
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0.18 mM, 43% inhibition of the activity with quercetin, 13% inhibition of the activity with o-dianisidine, isoenzyme POX II; 0.18 mM, 71% inhibition of the activity with quercetin, 95% inhibition of the activity with o-dianisidine, isoenzyme POX I
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individually grafted onto a novel CSG1.0 membrane as a ligand for enzyme purification
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25 mM, 20-30% inhibition
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weak inhibition at pH 8.5, strong inhibition at pH 10.0
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D-histidine oxidation
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inhibits reaction with dimethylhistidine
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inhibition is relieved by high concentrations of substrates
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competitive inhibitor of serine transamination
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10 mM: 56% inhibition with L-phenylalanine and pyruvate as substrates
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weak
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weak
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0.2 mM, 51% inhibition. 0.7 nmM, 93% inhibition
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strongly blocked SmARG-activity
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competitive inhibition, 10 mM
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1 mM, 20-30% inhibition
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5% inhibition at 4 mM
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L-His: activates in presence of Mn2+, strong noncompetitive inhibition without metal ion or in presence of Mg2+, Sr2+, Ca2+, Na+ or K+. D-His has almost the same effect as L-His
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L-His: activates in presence of Mn2+, strong noncompetitive inhibition without metal ion or in presence of Mg2+, Sr2+, Ca2+, Na+ or K+. D-His has almost the same effect as L-His
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about 40% inhibition at 10 mM
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enzyme YtmJKLMN shows 45% inhibition at 0.05 mM
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (30 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
3.4
-
pH 8.0, 26°C
0.0178
-
pH 8.0, 22°C, recombinant His-tagged enzyme
1.3
-
pH 8.0, 25°C
96.9
-
pH 7.0, 30°C

KM Value (108 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.34
-
pH 8.0, 26°C
5
-
pH 6.8
23
-
with pyruvate and NADPH as cosubstrate
6.1
-
-
0.45
-
-
0.195
-
-
0.0054
-
pH 8.0, 22°C, recombinant His-tagged enzyme
23.8
-
with 2-oxoisohexanoate, pH 8.0, 30°C
6.9
-
cosubstrate pyruvate, pH 8.9, 37°C
2.7
-
cosubstrate pyruvate, 37°C
18
-
pH 8.0, 25°C
22
-
-
2.2
-
-
8.14
-
pH 7.0, 30°C
0.0002
-
-

Ki Value (27 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.41
-
-
0.148
-
-
6.1
-
at pH 10.0
40
-
-
5.6
-
-
4.4
-
30°C, pH 8.0

IC50 Value (5 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.118
-
recombinant enzyme

References & Links

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Links to other databases for L-histidine

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ChEBI
PubChem
ChEBI
PubChem